5-Amino-2-methylphenol → HCID 69490164, compound

HRID 851912

Reaction equation

HRID 851912 reaction equation
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[CH3:20])[NH2:16].C(N(C(C)C)CC)(C)C>C(O)CCC>[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH3:20])=[C:13]([OH:12])[CH:14]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 69490164HCID 69490164, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

6-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.41 mmol), prepared as in reference 1, is mixed with 3-hydroxy-4-methylaniline (150 mg, 1.22 mmol) and diisopropylethylamine (213 μL, 1.22 mmol) in n-butanol (1.3 mL). The mixture is heated to 120° C. for 18 hours, with stirring. The reaction is then cooled to ambient temperature and the solvent is removed. The resultant crude product is purified by flash column chromatography using a gradient of 3-5% MeOH in DCM to yield 5-(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-2-methyl-phenol (92 mg; 70%).

Workup

  1. temperatureThe reaction is then cooled to ambient temperature
  2. customthe solvent is removed
  3. customThe resultant crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-89414035e14542ca8ed3140ee143d449
Source dataset
uspto-grants-2007_08
Patent number
US07253166B2

Linked notes

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